I don't understand the point he makes about forced discretionary spending. I have never bought a round of drinks at a bar, except in foreign countries where a round cost me less than $5. I don't ever feel like there's discretionary spending I'm forced to take. I either can afford it or I can't, and if I can't, I don't buy it and I don't feel guilty about it.

I buy other's drinks all the time. Never a whole round. That's ridiculous. Why he felt obligated to do that was left unsaid, but I doubt his reasons would convince me that he was actually forced to do that.

More generally, as you rise up the social ranks, you have to get more and more comfortable with gross differences in wealth and learn to be able to be comfortable with and accommodate socially those with so much more or so much less than you. This guy never seemed to learn that trick.

Were I buying a round of drinks and everyone else got $5 drinks and this one guy wanted a $20 drink, I'd have been like, "Ooh dude, can't really swing that, mind getting something cheaper?" If he does mind, just don't buy his drink. He's not going to get mad if you can't afford to buy him a drink.

Buying rounds at all, though, that's just insane if you need to keep a strict budget. It smacks of irresponsibility. If people are taking turns buying rounds, just opt out and pay for what you drink.